Pyridine → HCID 86735188, compound

HRID 1438958Notes

Reaction equation

HRID 1438958 reaction equation
[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:15](=O)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].Cl.[NH2:28][OH:29].N1C=CC=CC=1>C(O)C.O>[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH:13]=[C:14]2[C:15](=[N:28][OH:29])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 1012243beta-Acetoxy-5beta-pregn-16-en-20-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 86735188HCID 86735188, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

56 Parts of 3β-acetoxy-5β-pregn-16-en-20-one is mixed with 315 parts of ethanol and heated to reflux to effect solution. Then, 11.6 parts of hydroxylamine hydrochloride, 14.7 parts of pyridine, 11.2 parts of water and 395 parts of ethanol is added and the refluxing continued for 2 hours. Distillation is initiated and continued until the pot volume is about 200 parts. The pot residue is then chilled to afford a precipitate that is washed first with 150 parts by volume chilled distillate and then with 200 parts of water. Further cooling of the mother liquor affords a second crop. The first and second crops are combined to give 3β-acetoxy-5β-pregn-16-en-20-one oxime, in a yield of 83.4%. This compound melts at about 180°-183° C. and is represented by the following structural formula. ##STR3##

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. distillationDistillation
  4. temperatureThe pot residue is then chilled
  5. customto afford a precipitate that
  6. washis washed first with 150 parts by volume
  7. temperaturechilled distillate
  8. temperatureFurther cooling of the mother liquor
  9. customaffords a second crop

Sources & evidence

ORD record
ord-b759c17202a5450abf356dab3487f43e
Source dataset
uspto-grants-1977_11
Patent number
US04057543

Reaction notes

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